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How I Plan a Night in Tokyo: Dinner, Exploring and Bookings Without Clashes

Stagger dinner, Kabukicho, and Yoshiwara or outcall — the worst is drinking too much, rushing to a booking, arriving late and losing time.

Shinjuku East Exit in the rain — taxi queues get long

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I learned the hard way: having too much fun drinking in Kabukicho, I almost missed a booking. Now I plan the order of the night in advance.

Afternoon: confirm the evening's booking. If it was made the day before, reconfirm before going out.

Early evening: have dinner in Shinjuku or Ueno and go easy on the drinks. Show up drunk and you may be turned away — not worth it.

If going to Yoshiwara: allow enough time for subway plus walking or a taxi, and arrive a bit early. If outcall: get back to the hotel, check in, and wait at the agreed time.

Don't: stay out late in Kabukicho and then rush to Yoshiwara; check out of your only hotel before the booking is confirmed; or leave it past the last train without deciding whether to extend, take a taxi or call it a night.

Taxis are hard to get in the rain, so leave earlier. Weekends and holidays book up faster — lock in Yoshiwara or outcall slots early.

Planned like this, food, drinks, exploring and the main event all fit, and the whole night flows much better.